Cannabinoid conjugate molecules

Abstract

Disclosed are conjugate molecules formed from an active agent which is linked to a cannabinoid moiety through a specified linker having ester and amide end groups. The active agent can be a COX-2 inhibitor moiety, and the cannabinoid moiety can be a cannabidiol moiety. These conjugate molecules are contemplated to potentially be effective in the treatment of medical conditions.

The invention claimed is: 
     
       1. A method for synthesizing a conjugate molecule, comprising:
 receiving an aminohydroxyalkane having a protecting group on the amino group; 
 reacting the aminohydroxyalkane with a celecoxib molecule, forming a covalent bond between the aminohydroxyalkane and the celecoxib molecule to obtain a second intermediate molecule; 
 removing the protecting group from the amino group to obtain a primary intermediate molecule comprising the celecoxib molecule; 
 receiving a secondary intermediate molecule comprising a cannabinoid having a chloroformate group; and 
 reacting the primary intermediate molecule with the secondary intermediate molecule to obtain the conjugate molecule; 
 wherein the conjugate molecule has the structure of Formula (II): 
 
       
         
           
           
               
               
           
         
       
       wherein L is alkyl; and 
       wherein R is hydrogen or alkyl. 
     
     
       2. The method of  claim 1 , wherein L contains 3 to 5 carbon atoms. 
     
     
       3. The method of  claim 1 , wherein R is hydrogen or contains 1 to 3 carbon atoms. 
     
     
       4. The method of  claim 1 , wherein the molecule has the structure of Formula (II-a): 
       
         
           
           
               
               
           
         
       
       wherein R is hydrogen or alkyl. 
     
     
       5. The method of  claim 4 , wherein R is hydrogen. 
     
     
       6. The method of  claim 4 , wherein R is —CH 3 . 
     
     
       7. The method of  claim 1 , wherein the secondary intermediate molecule is prepared by reacting cannabinodiol (CBD) with TBDPSCl to form a protecting group on a hydroxyl group of the CBD and obtain the secondary intermediate molecule. 
     
     
       8. The method of  claim 7 , further comprising removing a TBDPS protecting group on the secondary intermediate molecule.